Tinidazole

Names

[ CAS No. ]:
19387-91-8

[ Name ]:
Tinidazole

[Synonym ]:
Bioshik
1-[2-(Ethylsulfonyl)ethyl]-2-methyl-5-nitro-1H-imidazole
Trimonase
Fasigyn
Fasygin
TINDAMAX
UNII-033KF7V46H
1-(2-(Ethylsulfonyl)ethyl)-2-methyl-5-nitro-1H-imidazole
MFCD00057217
Tinidazolum
1H-Imidazole, 1-[2-(ethylsulfonyl)ethyl]-2-methyl-5-nitro-
Simplotan
Tinidazol
Tinidazole
Fasigin
Tricolam
1-[2-(Ethylsulfonyl)ethyl]-2-methyl-5-nitroimidazole
Ethyl[2-(2-methyl-5-nitro-1-imidazoIyl)ethyl]sulfone
Symplotan
EINECS 243-014-4

Biological Activity

[Description]:

Tinidazole is a synthesized imidazole derivative used in antiprotozoal treatment with antiamebic and antibacterial properties.Target: AntibacterialTinidazole is a 5-nitroimidazole active in vitro against a wide variety of anaerobic bacteria and protozoa. Tinidazole is an effective treatment against anaerobic microorganisms based on its pharmacokinetic characteristics (C(max) 51 microg/ml, t(1/2) 12.5 h) and its excellent in vitro activity. Its long half-life allows once a day regimens. Tinidazole is as effective as metronidazole in the treatment of infections caused by T. vaginalis, giardiasis and amebiasis and bacterial vaginosis, malaria, odontogenic infections, anaerobic bacterial infections (pelvic inflammatory disease, diabetic foot), surgical prophylaxis (abdominal and hysterectomy) and Helicobacter pylori eradication. Tinidazole has recently been resurrected and FDA approved for trichomoniasis and BV in the USA and is being restudied as an alternative to metronidazole for BV. In vitro antimicrobial activity and pharmacokinetics studies indicate that when compared directly with metronidazole, tinidazole has minor but possibly relevant antimicrobial as well as pharmacokinetic advantages.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial

Research Areas >> Infection

[References]

[1]. Granizo JJ, et al. Tinidazole: a classical anaerobical drug with multiple potential uses nowadays. Rev Esp Quimioter. 2009 Jun;22(2):106-14.

[2]. Nailor MD, et al. Tinidazole for bacterial vaginosis. Expert Rev Anti Infect Ther. 2007 Jun;5(3):343-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
528.4±30.0 °C at 760 mmHg

[ Melting Point ]:
117-121 °C(lit.)

[ Molecular Formula ]:
C₈H₁₃N₃O₄S

[ Molecular Weight ]:
247.271

[ Flash Point ]:
273.4±24.6 °C

[ Exact Mass ]:
247.062683

[ PSA ]:
106.16000

[ LogP ]:
-0.27

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.599

[ Storage condition ]:
Refrigerator

[ Stability ]:
Stable. Incompatible with strong oxidizing agents.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NI6255000

CHEMICAL NAME :: Imidazole, 1-(2-(ethylsulfonyl)ethyl)-2-methyl-5-nitro-

CAS REGISTRY NUMBER :: 19387-91-8

BEILSTEIN REFERENCE NO. :: 0618182

LAST UPDATED :: 199612

DATA ITEMS CITED :: 20

MOLECULAR FORMULA :: C8-H13-N3-O4-S

MOLECULAR WEIGHT :: 247.30

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2710 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - cyanosis Gastrointestinal - changes in structure or function of salivary glands

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2720 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - cyanosis Gastrointestinal - changes in structure or function of salivary glands

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3 gm/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - cyanosis Gastrointestinal - changes in structure or function of salivary glands

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >250 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - cyanosis

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3200 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - tremor Behavioral - ataxia

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2730 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - cyanosis Gastrointestinal - changes in structure or function of salivary glands

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3940 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - cyanosis Gastrointestinal - changes in structure or function of salivary glands

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >250 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - cyanosis

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 60 gm/kg/30D-C

TOXIC EFFECTS :: Behavioral - tremor Kidney, Ureter, Bladder - hematuria Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 109 gm/kg/26W-C

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - changes in testicular weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3 gm/kg

SEX/DURATION :: female 9-14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 12 gm/kg

SEX/DURATION :: female 9-14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3 gm/kg

SEX/DURATION :: female 7-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 15 gm/kg

SEX/DURATION :: female 7-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 50 mg/kg

REFERENCE :: AIVMBU Archivos de Investigacion Medica. (POB 12,631, Col. Narvarte, Deleg. Benito Juarez, 03020 Mexico City, DF, Mexico) V.1- 1970- Volume(issue)/page/year: 15,311,1984

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H312 + H332-H341-H351

[ Precautionary Statements ]:
P261-P280

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xn:Harmful

[ Risk Phrases ]:
R20/21/22;R40

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
NI6255000

[ HS Code ]:
2933290090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933290090

[ Summary ]:
2933290090. other compounds containing an unfused imidazole ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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